Chloroacetone → HCID 86756528, compound

HRID 1531570Notes

Reaction equation

HRID 1531570 reaction equation
[C:1]([O:5][C:6](=[O:46])[N:7]([CH2:23][CH2:24][C:25]1[C:33]2[C:28](=[CH:29][CH:30]=[C:31]([NH:34][C:35]([NH2:37])=[S:36])[CH:32]=2)[NH:27][C:26]=1[C:38]1[CH:43]=[C:42]([CH3:44])[CH:41]=[C:40]([CH3:45])[CH:39]=1)[CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][S:19]([CH3:22])(=[O:21])=[O:20])=[CH:14][CH:13]=1)([CH3:4])([CH3:3])[CH3:2].Cl[CH2:48][C:49](=O)[CH3:50]>>[C:1]([O:5][C:6](=[O:46])[N:7]([CH2:23][CH2:24][C:25]1[C:33]2[C:28](=[CH:29][CH:30]=[C:31]([NH:34][C:35]3[S:36][CH:48]=[C:49]([CH3:50])[N:37]=3)[CH:32]=2)[NH:27][C:26]=1[C:38]1[CH:39]=[C:40]([CH3:45])[CH:41]=[C:42]([CH3:44])[CH:43]=1)[CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][S:19]([CH3:22])(=[O:20])=[O:21])=[CH:14][CH:13]=1)([CH3:3])([CH3:2])[CH3:4]

Participants

3

Reactant 2

HCID 6571ChloroacetoneHCID 86756529HCID 86756529, compound

Product 1

HCID 86756528HCID 86756528, compound

Procedure

To a solution of {2-[2-(3,5-dimethylphenyl)-5-thioureido-1H-indol-3-yl]ethyl}-[4-(4-methanesulfonylaminophenyl)butyl]carbamic acid tert-butyl ester (15 mg in 0.80 mL ethanol) was added 0.010 mL chloroacetone and the resulting suspension heated to reflux on an oil bath. After 5 hours, the mixture was cooled to room temperature and concentrated in vacuo. Purification of the residue by flash chromatography on silica gel (methylene chloride:methanol, 96:4) gave the title compound (15 mg).

Workup

  1. temperaturethe resulting suspension heated
  2. temperatureto reflux on an oil bath
  3. concentrationconcentrated in vacuo
  4. customPurification of the residue by flash chromatography on silica gel (methylene chloride:methanol, 96:4)

Sources & evidence

ORD record
ord-442409edddc949d7b815ec51c12894d5
Source dataset
uspto-grants-2001_03
Patent number
US06197975B1

Reaction notes

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